(Received 1 August 2013;accepted 12 August 2013;online 17 August 2013)

In the title compound, C26H26ClN3O2·C3H7OH, the benzimid­azole ring system is essentially planar [maximum deviation = −0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol­ecule links with the benzimidazole ring via an O—H⋯N hydrogen bond. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R22(28) motif. π–π stacking occurs between the parallel chloro­benzene rings [centroid–centroid distance = 3.792 (1) Å]. Weak C—H⋯π inter­actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.

Econazole, miconazole, ketoconazole, fluconazole and itraconazole possessing imidazole or triazole ring in their structures have been known as antifungal agents and used in clinics. The crystal structures of econazole (Freer et al., 1986), miconazole (Peeters et al., 1979a), ketoconazole (Peeters et al., 1979b), fluconazole (Caira et al., 2004) and itraconazole (Peeters et al., 1996) have been reported, previously. Then, similar ether structures possessing benzimidazole ring in their structures have been reported to show antibacterial activity more than antifungal ativity (Özel Güven et al., 2007a,b) and the crystal structures of these compounds have been reported (Özel Güven et al., 2008a,b,c,d). Lately, the crystal structure of a similar new compound has been reported (Özel Güven et al., 2013). Now, we report herein the crystal structure of the title compound, (I), which is another benzimidazole derivative.

In the molecule of the title compound, (Fig. 1), the bond lengths and angles are generally within normal ranges. The benzimidazole [A (N1/N2/C3—C9)] ring system is approximately planar with a maximum deviation of -0.018 (2) Å for atom C6 and its mean plane is oriented with respect to the benzene [B (C11—C16)] and phenyl [C (C17—C22)] rings at dihedral angles of A/B = 4.51 (6) and A/C = 56.16 (6) °. The dihedral angle between benzene and phenyl rings is B/C = 59.11 (7)°. Atom C10 is 0.059 (2) Å away from the plane of the benzene ring and atoms C1 and N3 are 0.052 (2) and 0.084 (2) Å away from the plane of the phenyl ring. The morpholine ring D (C23—C26/O2/N3) is not planar, but adopting a chair conformation with puckering parameters (Cremer & Pople, 1975) QT = 1.044 (6)Å, ϕ = 33.3 (2)° and θ = 58.6 (2)°.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric R22(28) dimers (Bernstein et al., 1995). These dimers are further connected via intermolecular O—H···N hydrogen bonds to the solvent molecules (Table 1 and Fig. 2). There also exists a π···π contact between the benzene rings, Cg3—Cg3i, [centroid-centroid distance = 3.792 (1) Å; symmetry code: (i) 1 - x, -y, -z; Cg3 is the centroid of the ring B (C11—C16)] and two weak C—H···π interactions (Table 1), in which they may further stabilize the structure.

The title compound, (I), was synthesized by the reaction of 2-(1H-benzimidazol-1-yl)-1-(4-morpholinophenyl)ethanol with aryl halide using sodium hydride. NaH (0.022 g, 0.557 mmol) was added to a solution of alcohol (0.180 g, 0.557 mmol) in DMF (4 ml) in small fractions. After stirring the mixture a few minutes, 4-chlorobenzylbromide (0.114 g, 0.557 mmol) was added. Then, the reaction mixture was stirred additional 4 h at room temperature. The reaction was stopped by adding a small amount of methyl alcohol. After evaporation of the solvent, dichloromethane was added to the reaction mixture and extracted with water. The organic phase was separated and dried with anhydrous magnesium sulfate, then evaporated to dryness. The residue was purified by column chromatography using chloroform and crystallized from isopropyl alcohol to obtain colorless crystals suitable for X-ray analysis (yield; 0.127 g, 51%).

Atom H3A (for OH group) was located in a difference Fourier map and was freely refined. The C-bound H-atoms were positioned geometrically with C—H = 0.98, 0.93, 0.97 and 0.96 Å for methine, aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = k × Ueq(C), where k = 1.5 for methyl H-atoms and k = 1.2 for all other H-atoms.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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